反应详情

A RB flask was charged with 4-aminotetrahydropyran (9.77 g, 97 mmol) in THF (480 mL) and was cooled in an ice bath. To this stirring solution was added 2-chloroethyl isocyanate (11.19 g, 106 mmol) drop-wise and the reaction was brought to RT and stirred at RT overnight. The reaction mixture was concentrated to dryness and the crude product was washed successively with saturated NH4Cl (60 mL) and saturated NaHCO3 (60 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated to dryness to afford a white solid. Toluene (20 mL) was added and the residue was concentrated to dryness. The process was repeated a second time (to remove any moisture) to afford 1-(2-chloroethyl)-3-(tetrahydro-2H-pyran-4-yl)urea as a white solid. The product was utilized in the next reaction without purification. 1H NMR (CDCl3): δ 5.34-4.94 (bs, 1 H), 4.93-4.56 (bs, 1 H), 3.94 (dt, J=11.9, 3.2 Hz, 2 H), 3.84-3.71 (m, 1 H), 3.64-3.59 (m, 2 H), 3.49-3.47 (m, 2 H), 1.95-1.83 (m, 2 H), 1.50-1.34 (m, 2 H); MS (ESI) m/z: 207.1 (M+H+).

1. temperaturewas cooled in an ice bath
2. customwas brought to RT
3. concentrationThe reaction mixture was concentrated to dryness
4. washthe crude product was washed successively with saturated NH4Cl (60 mL) and saturated NaHCO3 (60 mL)
5. dry with materialThe organic layer was dried over anhydrous Na2SO4
6. concentrationconcentrated to dryness
7. customto afford a white solid
8. concentrationthe residue was concentrated to dryness
9. customto remove any moisture)